Good Dates Gone Wrong

October 18, 2023 | Nia Williams

Good Dates Gone Wrong

Dating is such a hit-and-miss game these days. That’s why first-date impressions are so important. These people share their unfortunate stories of how their first date got instantly ruined by the other person. From inviting their parents to having their boyfriend show up, it’s hard to believe that people like this actually exist. But yeah, they do.

1. Not Staying For A Refill

She confided in me about her severe anxiety in public spaces, proposing that she could cook dinner instead. Before settling on the plan, we took a walk to decide whether dinner would follow. She was incredibly excited about the prospect of cooking after our walk.

The food was delightful and she suggested a movie. About a quarter of an hour in, she gently bumped into me and initiated a make-out session. As things started heating up, something nudged my shoulder. I was lying on top of her by then—and I was caught completely off-guard.

Surprised, I spun my head around to find a four to five-year-old boy staring back at me, asking if he could get a glass of water. His mother immediately began berating him, ordering him back to his room, which he obeyed. She quickly apologized and tried to resume our kiss.

I asked her to give me a moment. I filled a glass with water and called the boy back out. When he returned, I handed him the water. After gulping down and expressing his gratitude, he scampered back into his room. The fact she hadn't mentioned having a child there and also berated him for something as basic as a request for water made me quite upset.

I decided to leave after that incident, making a personal vow to never behave that way as a parent toward my future kids.
Young parents are arguing with boy ,covering his ears with hands.bearfotos, Freepik

2. A Sign To Move On From HIM

I was once on a delightful date with a guy when he noticed a distinctive copper bracelet on my wrist. I shared with him the significance behind it—it was an endearing souvenir I picked up during my study term in South Africa, gifted by a local resident.

The piece was a strong band of copper with strands of the same metal entwined in the centre. Curious to examine it more closely, he asked to see it, so I removed it and handed it over. To my surprise and dismay, he broke it in two, mistaking its woven copper heart for a spring mechanism. 

As if that wasn't enough, he told me it was time for me to let go of my past and not linger on my South African memories, noticing my visible sadness.

Seriously, what? Needless to say, we never exchanged words again.
Man is arguing with woman outside.Keira Burton , Pexels

3. Jaw-Dropping Moment

I recently had a dinner date with a stunning lady. We had loads to talk about and our conversation went on for almost an hour.

As the time to hit the arcade drew near, I asked the waiter for the bill intending to cover our meal. However, she placed her card alongside mine, offering to pay half. I assured her it was okay for me to cover it, but she resisted.

She insisted on covering her part of the meal. Fast forward to later that night. After spending quality time at the arcade, we were heading back to our cars. She turned and said, "I don't think we are a good match". I asked, "Oh, why's that?" And then she dropped the bomb—"I thought as a man, you'd pay for our dinner tonight".

I can only imagine the shocked expression on my face at hearing those words. What was I suppose to do… snatch her credit card and toss it back at her?andreas , Freepik

4. Three’s A Crowd

We enjoyed our first dinner date then decided to pop into a nearby bar for a drink or two.

While there, one of her work colleagues spotted us and came over for a chat. This coworker decided to pull up a chair and join our table. It was fine at first, but pretty soon, all the chat turned into work-related topics and office gossip.

I felt a little out of the loop as there wasn’t much I could contribute to their work-focused conversation aside from diverting the discussion completely. After listening in for about 45 minutes, I mentioned that I was tired and opted to call it a night. But the cherry on top was still to come.

On my way out, I noticed a few of my buddies strolling into the same bar. Under normal circumstances, I would have loved to hang out with them. But I committed to leaving to maintain my 'tired' cover and because she had already tried to persuade me to stay.

Young bearded man is seating at bar with friends having a drink.cottonbro studio , Pexels


5. I’m Dang-Near Speechless

The first date we had was truly unforgettable. I often catch myself looking back on that amazing night, envisioning a wonderful impending life change. 

But right before our scheduled second date, I received a voicemail that changed everything: "Just so you know, you were on a date with my soon-to-be wife last night. I'm not blaming you because you probably had no idea I existed—but I do. I'd be grateful if you could stop dating her".

There you have it.

Sad man is seating on the sofa and talking on the phone.RDNE Stock project ,Pexels

6. I Swear I Didn’t Plan That

We were enjoying dinner that evening, everything was great. After wrapping up, we found ourselves strolling down a dimly lit sidewalk deep in conversation. Suddenly, she bumped straight into a signpost we both failed to spot. I involuntarily chuckled before I could muffle it. 

She then teasingly blamed me for setting up the whole scenario just for a laugh.

Elegant young couple is standing by the light post at night.freepik, Freepik

7. Don’t Cross My Boundaries

I once went out bowling with a guy along with a few other friends. We were all having a good time, until it was my friend's turn to bowl, and I found myself sitting alone with this guy. That's when he decided to put his hand on my thigh.

I have a thing about personal space, especially with people I've just met. Feeling uncomfortable, I subtly moved his hand away, trying not to make a scene.

His initial move wasn't really a problem—after all, he was just trying his luck, right? But what really made me mad was his reaction. He put his hand back on my leg, gripping it firmly. Assuming he didn't get my hint earlier, I calmly took his hand and put it back on his lap.

He gave me a glare, then shockingly put his hand on my inner thigh. I reacted quickly, taking hold of his wrist, pulling his hand away and giving him a stern, silent "no" with my expression. Needless to say, we didn't have a second outing. If a man can't respect my personal space in public, I have no reason to believe he'll respect it in private.

Young couple are seating at bowling alley next to bowling balls.cottonbro studio , Pexels

8. This Smells Off

We were enjoying our first date in a posh dining place. It seemed to be the perfect evening, with delightful dinner and engaging talks. However, that's when he decided to make an off-putting move—he proceeded to silently slide off his shoes and inch them towards me under the table.

Whoa! Those shoes smelled terrible! So, I tried to give them a nudge back in his direction with my foot. But, undeterred, he just continued the conversation and slyly slid them back towards me.

Seriously, who in their right mind decides it's a good idea to remove their shoes in a fancy place like this? And push them towards their date, of all things? And wouldn't you think they'd address the issue of stinky shoes first?

Woman is looking around at restaurant.Katerina Holmes, Pexels

9. We Just Met

He asked if I could be exclusive because his latest ex-girlfriend was unfaithful, and he wanted reassurances that any new relationship would be monogamous. I completely understand this, as I prefer monogamy myself. However, this conversation occurred only half an hour into our initial encounter.

We were just having coffee after matching on a dating app a few days before. And to be honest, I wasn't even talking to other guys at that point, but I wasn’t too keen on letting a guy I just met dictate my actions. I certainly didn't want to be with someone who was allowing his ex's behavior to influence his expectations and feelings toward me.

That said, I do wish him the best and hope he's been able to recover from that past relationship.

Couple are seating and drinking coffee outside.Vlada Karpovich, Pexels


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10. First And Last Date

I recently went on a first date with an intelligent and stunning woman I connected with online. Over several weeks, we had developed an excellent friendship.

Things were sailing smoothly on the date. There was a clear romantic connection between us, we shared a lot of common ground, and thoroughly enjoyed our evening together. Post dinner, we chose an elegant lounge to continue our night, talking about our lives, laughing, sipping our drinks, and playfully flirting for an additional few hours.

The topic of our conversation soon moved towards our shared experience as single parents and specifically about our daughters, who were about the same age. 

This was a subject we had explored during our online chats, and so it seemed quite fitting that she would share a photo of her daughter and I felt inclined to reciprocate. But that's when things went off track dramatically.

Almost out of nowhere, she looked at my daughter's picture, actually named her—a detail I hadn't shared—and dropped the bombshell that our daughters already were acquaintances, regardless of the one-hour distance between where they lived. 

As if that wasn't enough, she then casually added that she was also familiar with my ex due to a common friend. At that point in time, my relationship with my ex was quite strained. Consequently, what had appeared to be a promising and delightful first date, transitioned abruptly into our first and last encounter. We haven't crossed paths since.

Couple are drinking coffee and looking at cell phone.gpointstudio , Freepik


11. No Idea What Happened

During my first week of college, I summoned the courage to ask a Korean exchange student on a date. This was a first for me, so you can imagine my surprise when she agreed. Especially since she was stunningly beautiful and completely out of my league.

A couple of days after, I drove to her dorm in my relatively new Mustang. She was quite silent, which I attributed to her being shy. We hit the highway, cruising at a steady 55 miles per hour, when disaster struck out of nowhere. All of a sudden, she wound down the window and regrettably spewed everything—and I mean everything—on the outside of my car.

It honestly seemed like she'd consumed an entire gallon of vegetable soup prior to our date. Without delay, I drove her back to her dorm. She hurried out of the car, leaving me alone to take care of the mess. In the aftermath, even a trip to the car wash couldn't help; my car's paint was faded from the incident.

Remember, this was a time before the common use of mobile phones, so tracking her down afterward was tough. Despite my efforts, I never saw her again after that day. That incident took place back in 1990, and to this day, I'm still clueless about what happened.metamorworks, Shutterstock

12. That Was Unexpected

I was about 22 or 23 when I had my first date with this guy at a dinner place. When I arrived, my jaw dropped. I noticed two additional people at the table. As it turned out, he had brought his parents along to our date!

Quietly, I excused myself claiming a bathroom break and then beat a hasty retreat. Talk about an uncomfortable situation.freepik, Freepik

13. There Won’t Be Seconds For Me

I matched with this guy on Tinder and we hit it off in our chat. He seemed really nice and definitely had a cool personality! We decided to meet in person and grabbed a drink together. He was dressed well, made me laugh, and it looked like he was into me. We decided to continue the evening somewhere else with a bite to eat.

On the way though, we stopped at a convenience store because he needed chapstick. No big deal, everyone needs chapstick every now and then, right? But that's where things took a turn for the worse. He bought the chapstick, opened up the packaging right at the counter, and dumped the box in front of the checkout clerk. 

The clerk and I exchanged baffled looks. Politely, the cashier pointed out the trash bin by the door and asked him to discard his waste there. The guy huffed, rolled his eyes, and finally tossed the wrapper. That's when I realized that a second date wasn't on the cards for me.

There were more hints of his inconsiderate nature at the next place too, but that incident at the store was the moment I was fairly certain he lacked basic manners.

Couple are walking inside a store and looking something on the shelfs.i_am_zews, Shutterstock

14. Dinner Ended Along With My Interest

When my marriage ended, I decided to start dating, looking to meet fresh faces.

In the early stages of dating, I preferred low-risk, casual activities like grabbing a coffee as a first meet-up. If things turned strange, I had the option to politely exit.

So, on one of these dates, the woman unexpectedly brought along her two little ones, whom I wasn't even aware of. However, it wasn't a big issue for me, and she was really pleasant. 

After chit-chatting outside the coffee place for around twenty minutes, I suggested we switch the setting to a more child-appropriate spot like an ice cream parlor. Everyone was on board with this idea.

We located a nearby place and made the move. Ice creams kept the kids delighted, and our conversation continued to flow nicely for almost an hour. I then put forward the idea of catching up for dinner. She agreed, but mentioned it would need to be later in the evening and that her kids might have to tag along as her babysitter had cancelled at the last minute. 

That night, we met up at a budget-friendly steak restaurant. The rapport was good and conversation lively. However, after downing three drinks at dinner, she became quite tipsy and disheveled, and decided to drive her children home. I proposed footing her cab fare home, which she declined. 

That was the final straw for me.

Woman is smiling and making a toast at dinner seating next to her daughter.freepik, Freepik

15. Those Aren’t Tears Of Joy

I met a single mom at Denny's. We were both getting along pretty well, talking about our families and things. I mentioned that I didn’t get along with my dad because he's a narcissist. That’s when she said, "So is my ex" and immediately started crying.

For the rest of the date I was her psychologist.

Man is standing next to a crying woman and looking at her.Pavel Danilyuk , Pexels

16. Front Row Ticket For One

The date was a success. We chatted up a storm at a local bar. After that, she extended an invitation for me to join her at her place, just a short distance from the bar.

Once we stepped inside, she inquired about my movie preference. I realized I hadn't watched The Prestige yet, and recommended that. Little did I know that very choice would ruin our date.

Surprisingly, the film was so captivating, I found my slightly buzzed self turning down her flirtatious moves. I wasn't going to risk missing out on the best parts of the movie!

Couple are seating on the bed and watching a movie.cottonbro studio , Pexels


17. Too Much Attention

I once dated this fella who ran a hip local business and was sort of a hometown hero. Now, I'm a fairly reserved type who's more comfortable blending into the background rather than being in the spotlights.

On our second rendezvous, we tucked into a cozy little eatery. It wasn't high-end but it had a dash of charm, perfect for a date night. During our feast, our table turned into a revolving door with five different folks, all his patrons, popping by for a chat.

He danced a fine line trying to be present with me whilst not shunning his clientele. Needless to say, it was awkward. Understanding my inborn shyness, he apologized and proposed we switch up our game plan. 

We'd finish up our meal, grab a few beverages and a little something sweet from a store and migrate to the beach, likely a less populous spot.

The store we swung by wasn't devoid of fans either: two more joined in for a chat. And it didn't end there; at the waterfront, one more person cropped up and practically tried to plant themselves next to us. 

That's when I felt this arrangement might not be my cup of tea. I genuinely admired him but all the public attention was overwhelming. But wait, there's more to it.

Somehow, he sweet-talked me into a third outing and boy, am I glad he did. Fast forward two decades and we're still going strong. He's nudged me out of my bubble and I've guided him into relishing the joys of introverted respites and crowd-free weekends. He is my rock and my love for him is boundless.

Young woman is seating on the beach next to a man wearing blue jacket.Beata Nykiel, Pexels

18. Letting It All Out

We were really enjoying ourselves. Sipping on a few cocktails, sharing non-stop laughter and light-hearted flirtation. I don't recall ever clicking so quickly with someone before.

I was fresh back from my stint in Afghanistan and hadn't been home long. She queried about the weather conditions over there. Barely two minutes into the conversation, I found myself shedding tears and unleashing an outpour of emotions that had been pent up for so long.

She was unexpectedly handed all the gritty details she hadn't bargained for. The conversation turned so awkward that she was essentially trapped as I continued to talk and cry for almost two hours straight.

So our evening turned from an hour of amusing drinks into one and a half hours of emotional venting.

Man is crying and talking with girl.SAULO LEITE , Pexels

19. Poor In Judgment As Well

As soon as my date arrived, he jumped straight in and asked what I'd like to drink. A stout was my pick, but after a quick bathroom break, I came back to a different drink on the table. When I queried about the switch, he simply said the one he'd gotten was less expensive.

Well, alright then. It was a bit of a head-scratcher, but considering he was a student, I brushed it off. The topic of conversation veered towards how cash-strapped he was. 

Having my own monetary struggles, I felt an unexplained pang of guilt and ended up covering our expenses for the night. I didn't really mind, he was a pretty cool guy and we had quite a bit in common.

When it was time to head home, he accompanied me to my bus stop. Out of the blue, he whipped out a $20 bill and off he went to grab a kebab, without even offering me one. Inside, I was wincing at the whole situation. It was clear to me—our paths wouldn't cross again.

Once home, I received an unexpected image from him with an invitation to meet up again. Needless to say, a second rendezvous never happened.

Young woman is seating on the table with man ,drinking coffee together and smiling.NATASHA LOIS , Pexels

20. Bored Of Games

It was a pretty good night to start with. We were at a local bar, enjoying some drinks. Out of the blue, she suggested we play a round of Scrabble. She was a big fan of the game, it turns out. Truth be told, I'm not the best at it. Plus, I'd already had a couple too many to drink. I was really not up for a game of Scrabble.

She kicked off with a fancy word that made me sigh: "behooves". And there I was, struggling to come up with just "hat". That took all my allocated time. She followed by dropping “incredulous” on the board, while I could only muster “fun”. This back and forth continued right up until the end of the game.

We didn't play another game after that. In fact, we didn't even have another night out.

Toy bricks on the wooden table with word Racool_studio , Freepik

21. Beautiful But Rattled

During a blind date with a lady who recently came out of a difficult relationship, she arrived quite shaken up. While she was attractive, her turbulent mental state was evident. Inquiring about her well-being, she reassured me that she was alright.

However, when a tall man walked too close to her chair in the restaurant, she nearly leaped out of her seat. Eventually, she bravely spilled the beans about her troubling love life. She had been romantically involved with her cousin. Despite being deeply connected, she put an end to it, knowing it wasn't right.

He was disconcerted by the breakup, and honestly, she didn't seem too pleased, either. It was quite unfortunate—she was strikingly beautiful but wholly distant throughout our date. Upon concluding the evening, I drove her to her apartment building.

As we pulled up, I spotted a tall, handsome man casually leaning against a car out front. She gasped and identified him as "the cousin." Concerned, I offered to accompany her inside or drive her elsewhere if she preferred. She reassured me that she would be fine but subtly suggested I leave immediately.

Without missing a beat, she practically sprinted into his waiting arms as he approached us. As I drove away, I witnessed her climbing into his sleek Tesla.

Young couple is seating in the car and looking outside.freepik, Freepik

22. Never To Be Seen Again

Once dinner was done, we headed to a bar. The evening was going smooth—great chats and even had a make-out session. But with the bar filling up, we thought it'd be best to continue at my place. Before stepping out, I needed to use the men's room, and she decided to wait for me outside.

Done with my pit-stop, I came out to find her, catching a glimpse just in time to see her hop into the back of a pickup filled with people, speeding away.

Sometime later, I got a text from her—apparently, she had run into her best friend and had headed off to a party. Unfortunately, they didn't want me tagging along. After that night, she never crossed my path again.

People are dancing in the back of a blue pick up truck.Jacob Lund, Shutterstock


23. Painful Slip Up

In my college years, during the final week leading up to winter break, we connected via a dating app. Discovering that we were practically neighbours, we decided to grab coffee at a cafe that was just around the corner. 

After the caffeine kick, we thought it would be nice to stroll through the city. Given it was the height of winter, we found ourselves navigating through snow and ice.

During our walk, I cracked a joke that she found amusing and she playfully nudged my arm. Little did I know, that simple gesture would drastically alter my life. Unfortunately, I was standing on a slick patch of black ice when she nudged me. I lost my footing, slipped, and ended up tearing my ACL and MCL.

I was confined to crutches for the ensuing six months. It's not really her fault, but it's an understatement to say that incident put a damper on our date.

Young couple are walking outside on a road with snow.Leah Kelley, Pexels

24. The Look Of Panic

After my divorce, I embarked on my first date. Bless that unsuspecting man. Little did he know the waters he was treading in. Every classic 'don't' on a date checklist was horrifically met: I wouldn't stop talking about my former relationship and I overconsumed alcohol. To say I was a disaster would be an understatement.

Things took a turn for the worst as he was heading home. I incessantly questioned him about whether he intended to phone me. The sheer terror in his eyes is still a vivid memory. Needless to say, he never dialed my number. Consequently, that was our one and only disastrous outing. Charlie Foxtrot.

Woman is standing and looking back next to a man at bar.cottonbro studio , Pexels

25. I Got The Hint

We were enjoying drinks and some engaging chat, after which we decided to grab a bite at a late-night sub joint. The mood was light and playful, then out of the blue, a tipsy guy wandered by our table, stopping to take notice of her.

He boldly asked her, "Hey girl, can I have your number?" He then addressed me, "Sorry dude, are you with her?" Suddenly, I was at a loss for words. It felt wrong to say 'No' as if I was rejecting her, but 'Yes' would have been a lie.

Unsure of how to navigate this awkward situation, I settled for, "We just met". He moved on, repeating, "My bad—bro, don't set me off," over and over. The incident put a dampener on our lively chat. She wanted to head home and declined my offer to accompany her to her car.

The following day, I texted her, stating how much fun I had and apologizing for the awkwardness that capped off the night. I suggested we might catch up over coffee soon. Her reply was a simple 'Sure'. I said, "Great, I'll touch base soon." Her response was an unenthusiastic 'Great'. This brevity, a change from her previous texts, served as a clue.

Man is looking sad ,seating next to a girl looking at side.cottonbro studio , Pexels

26. That’s Not Cool

I once had a pleasant date with a lady. The next morning, as I was giving her a ride home, we had a chat about her long commute. Interestingly, she didn't seem concerned about it, even stating she'd drive under the influence if needed. I questioned why she'd make such an unsafe choice.

She shrugged it off, saying she often did it back in Idaho and was almost expecting a DUI ticket at some point. Now isn't that something?

Young man is driving a convertible car with girl seating next to him.Roberto Nickson, Pexels

27. Ultimate Turn Off

I connected with a good-looking guy through a dating app and we agreed to meet at a nearby Indian restaurant—my absolute favorite cuisine.

Our chemistry was off the charts during the conversation; lots of laughter, a bit of flirting from both sides. He was overwhelmingly attractive, in great shape, and had a sound financial status—he ticked all the boxes. However, things took a turn when he began mocking the waiter.

He started joking about the waiter's accent, how he moved, and his manner of speaking. I was stunned and upset, and it probably showed on my face because, at one point, he asked, "What's wrong?"

I told him straight up that I found his behavior inappropriate, but he brushed it off as harmless fun. I corrected him, saying it wasn't fun at all. As we parted ways in the parking lot, I tried to pay for my part of the meal, but he wouldn't allow it. Instead, he quipped, "Well, butterfly, you owe me dinner."

No, I don't owe you a thing. It was such a turn-off.

Woman is standing and looking at young black man who is looking at side upset.Dziana Hasanbekava, Pexels

28. Now That Was Rude

We were out on a date, and we were having fun, or so I believed. But then one of her pals turned up and suggested they catch a live band playing nearby. She thought it was a great idea—but I wasn't prepared for what she did next.

 She just left, without asking me to come along. She didn't apologize, invite me along or suggest we meet another time. Nothing at all. I understand if she wasn't enjoying the date, but a little politeness wouldn't have hurt.

Young man is seating alone and drinking coffee.Balljinder Singh, Pexels

29. Too Weird For Me

Around 15 or 16 years ago, we visited her place and started viewing Fight Club. The movie seemed pretty catchy back then.

As we were getting cozy, she abruptly yelled at me to "HALT"! I quickly checked if everything was fine. She just gestured for silence and refocused on the movie. We were at the scene where Brad Pitt sizzles Edward Norton's hand using chemicals.

There I was, trying to maintain our intimate moment. But her attention was entirely absorbed in the movie; she seemed hypnotized. Once that scene ended, I asked her about the sudden change in her behavior. After a sequence of probing, she made a shocking confession. 

She said she had a liking for watching people suffer pain, but she wasn't into causing it or experiencing it herself. Understandably, I never hung out with her after that.

Young man is looking at camera with surprised face.cookie_studio, Freepik

30. Yep, I’m Outta Here

I had recently turned 18 during my high school year when I started chatting with this girl I came across on Tinder. On our first date, everything seemed to run smoothly. We found out that we both shared similar taste in music and movies, and we both loved animals, among other things.

In the middle of our conversation, I decided to ask what she did for fun the previous week. She mentioned having a total blast getting extremely drunk with her friends over the weekend. Though I wasn't legally old enough to drink at that time, I wasn't against dating someone who drinks. I let her continue with her story, maintaining the flow of our conversation.

As the date progressed, I asked her about her plans for the upcoming weekend—I was hinting at arranging another date. She said that she intended to hit a club and spend the whole weekend getting extremely intoxicated with her friend.

Well, okay then. I asked, "What about the weekend after that?" She answered that she planned to get very drunk with her friends at yet another club. At that point, for me, it was clear enough that we probably weren't a suitable match. I promptly wrapped up the date and took my leave.

Young couple are seating and having a breakfast outdoorSamson Katt , Pexels

31. Freaking Out

Here's the story: I once went on a date with this charming, intelligent, hilarious, and polite guy. Things were sailing smoothly on our coffee date—we were chuckling and really hitting it off, when his ex-girlfriend unexpectedly walked in.

Immediately he saw her and panic set in. Over and over again, he exclaimed, "We need to leave. We need to leave." He was so rattled about the whole situation. As you'd expect, we made a swift exit. However, I must say, that was our first and last date.

Young woman is having a coffee in coffee shop with man looking at her.Juan Vargas, Pexels

32. That Was Super Uncomfortable

While we were out shopping for meals and treats, he cracked a peculiar, suggestive joke. He mentioned something along the lines of "I've got a special treat for you later" followed by a burst of self-amused laughter. That was cringey enough, but not at all the worst part of it—several bystanders caught wind of his comment too. 

I found it very off-putting because I prefer to take things slow, especially when it comes to relationships. This experience made me lose interest in him in no time at all.

Young woman is looking at side with surprised face.Polina Zimmerman, Pexels

33. So Distasteful

This guy acted rudely towards our waiter, and then expected praise for his behavior. When he saw that I didn’t approve of his actions, his response was just absurd. His idiocy didn't stop. He just turned his gaze away while still clearly showing annoyance towards both the waiter and me.

I directly handed the payment and a generous tip to the waiter, said I was sorry for the unpleasant situation, and made a swift exit. Not cool.

Couple are arguing with a waiter who is standing next to a table.Fancy Studio ,Shutterstock

34. Let’s Cut This Date Short

The day started off like any other. I was new in town, looking for a good time, and I found him on Tinder. He was my tour guide to a variety of local bars he favored.

But then, right in the middle of our date, he drastically changed. We were just strolling towards the next pub when he suddenly became hostile, peppering me with snarky comments. His main gripe? “You women can't stand short guys like us”.

I was utterly floored.

Yes, he was shorter than average, but I never made an issue of his height. I didn't emphasize something that wasn't of importance to me. I was there – ON the date! I knew his stature and willingly tagged along. I genuinely thought we were enjoying ourselves. It's not like he made a move and got rejected.

Up till today, I'm puzzled about what triggered his outburst. Did he anticipate me spontaneously swooning over him? Was I expected to cut the date short and start flirting aggressively with him?

After his outburst, I stood there, stunned. I was the woman who took a shot with him. Finally, with tears in my eyes, I said, “I thought we were doing well, but you've really made me feel rotten” and I dashed away, leaving him behind on the sidewalk. I immediately blocked him, recognizing his irrationality.

I pity him, but not to the extent that I'd endure disrespect when I did absolutely nothing to warrant it. Now ask me why I've only been dating tall, self-assured men since then.

Black couple arguing outsideKeira Burton , Pexels

35. You Thought Wrong

There was a great deal of playful banter and suggestive hints before our date. On the date itself, there was even more teasing, our arms brushing against each other, and our hands intertwined. We even mentioned having a cozy movie night complete with extra snuggling.

When our evening was wrapping up, I walked her to her car and inclined to give her a kiss. Suddenly, she seemed anxious so I retracted before I got too close. She stuttered, "Oh sorry. I was just uh..." and took a moment. I was left puzzled for a bit. She then stammered, "...I thought you were gay!"

I immediately questioned all the flirty signals, and she retorted, “Yeah, I don’t know—I typically don't act this way with my gay friends. I apologise."

Her comment left me in such a daze that I just muttered, “Okay, take care” without trying to resolve any misunderstanding. To be fair, it wouldn’t be absurd if someone perceives me as gay, but it also didn't match with anything that took place prior.

Woman is talking to a man wearing black leather jacket standing next to a car.RDNE Stock project ,Pexels

36. Stakes Were Too High

Our initial online chats were absolutely amazing, we clicked right away. Yet, on our very first face-to-face outing, she outright told me within a quarter of an hour at the dinner table that I'd need to be totally and irrevocably dedicated to her from that point forward.

When I tried to clarify her stance, her follow-up a statement was rather startling. "It's either you consent to be with me eternally, we'll head back to my place for a steamy night of passion so I can conceive, or we can end this dinner here and now," she told me.

While a night of romance was tempting, the associated gamble was much too great. I settled the bill and beat a hasty retreat.

Young man is seating on table with a girl and drinking red wine.Katerina Holmes, Pexels

37. The Truth Is—

During our fifth dinner date, I chose to share about my journey with anxiety and its impact on our relationship. However, he interrupted me, asking loudly, "So, your 'anxiety' is the reason you aren't comfortable being intimate with me?"

Then, he left me all alone at the restaurant, even though he was my ride home.

Young woman is seating alone at restaurant with sad face.Beyzanur K. ,Pexels

38. Act Your Age

During our date, my partner seemed uncomfortable at the sight of my blonde leg stubble and me mentioning the natural phenomenon of menstruation. It wasn't an in-depth discussion or anything—I just brought it up naturally as the conversation mirrored its significance.

Interestingly, my date is a second-year medical student. It's puzzling why he would react immaturely to such routine biological occurrences. His reaction truly seemed misplaced and immature.

At 25, he reacted to a tiny bit of 2-day old stubble on my legs with a distasteful "eww". It makes me wonder how he'll adapt in his future medical profession with such reactions.

Young bearded man is making disgusting face.wayhomestudio ,Freepik

39. Adios, Princess

Once my date showed up, everything seemed to be falling into place. She was pleasant, and we began connecting. However, when we began to place our orders, she asked the waiter about the best cabernet they offered, insisting he confirm it's from the top selection.

The waiter glanced at my modest attire and replied tersely, "What's listed in the menu is what we have." She spent the rest of the evening sulking. I decided that it was best to ask for split bills, which nearly drove her up the wall.

She retorted, "You're the man here, and it's your duty to foot the bill. If you're too broke to pay, perhaps we shouldn't be going out again!" I must say, my response was rather fitting, "I'm way ahead of you on that." Without further ado, I paid the bill and made my exit.

Young woman is arguing with a man seating at restaurant.Roman Kosolapov, Shutterstock

40. You’ve Got It All Wrong

I normally aim to be polite to everyone, commonly holding doors open for both genders.

During our outing, I held a door open for her, which surprisingly sparked a bit of an argument. Her reaction was ridiculous—she took it as me suggesting that, as a woman, she wasn't capable of opening her own door. 

This left me somewhat baffled as I only ever consider it an act of kindness. In fact, I really like it when others do the same for me. Well, it turns out, we didn't end up having a second date.

Man in grey suit is opening door for woman in grey suit to enter and smiling.Dmytro Zinkevych, Shutterstock

41. You Couldn’t Wait To Tell Me

I took a lady friend out for a date to our town's own zoo. When winter hits, they deck the whole area out in twinkling Christmas lights. It's not just lights—there's a light show and even a Ferris wheel. It makes for a truly charming date during the colder months.

So there we were atop the Ferris wheel, hand in hand, gazing at the sparkling lights beneath us. I turned and asked if she was enjoying herself. She gave me a nervous glance and dropped a bomb, "I've been seeing someone else. I mentioned our date and he got there first."

Talk about uncomfortable. I wish she waited till after the ride ended to break the news.

Couple is taking a selfie on cellphone against illuminated Ferris wheel.Depiction Images, Shutterstock

42. I Need A Breath Of Fresh Air

I went on a date once, and the guy arrived with super stinky breath. The date was actually going quite well, but it's such a downer when you meet somebody for the first time and they didn't even take the trouble to freshen up.

To be honest, I might have leaned in for a kiss, maybe even more, if only his breath didn't remind me of him munching on tiny chunks of poop before our inaugural rendezvous!

A girl is looking at side and holding her nose.karlyukav, Freepik

43. An Ugly Moment I’d Like To Forget

All this happened back in my high school days. She had invited me over to her house for a meal with her family, a group of people I hadn't gotten to know very well yet.

We found ourselves discussing old-fashioned names which we didn't find quite appealing. Each one of us began suggesting a few names that we thought were, shall we say, less than glamorous—like Gertrude, Bertha, and Eugene. 

And then I did the unthinkable. I said in quite an unpleasant tone, "I suppose not many names can beat Deborah in the lack of appeal!"

Little did I know, her mother was named Deborah. Her grandma was also present at the dinner table with us. But here's the kicker—we've been happily wedded for nearly seven years now!

Man is talking at family dinner.Askar Abayev , Pexels

44. Funny Mix-Up

My aunt arranged a date for me. Being half Asian and half European, when I visited my family in Asia, they had the inclination for me to date and hopefully marry this girl from a wealthy family.

We set up a rendezvous at a restaurant. The girl brought along her brother, who was accompanied by his girlfriend. I tagged along with a cousin of mine who was laughing at the whole situation. We did the introductions but with the noise in the place and their soft-spoken nature, I couldn’t catch their names.

My reluctance to re-ask their names out of concerns of appearing impolite was the first misstep. Anyhow, I started chatting with who I believed was my date. She was attractive and well-versed. I began to think—Hey, maybe this wasn't such a bad idea after all. Our conversations meshed well.

As our flirtation progressed, I thought she was enjoying it. But then abruptly the brother said something, and both he and my supposed date swiftly exited without any explanation. I was left bewildered. The plot twist was that I had been charming the brother’s girlfriend all along and not my actual date!

I had practically ignored my date from the moment we greeted each other.

Asian couple are having a lunch.cottonbro studio , Pexels

45. In Your Dreams

So, I hung out with a girl I work with as friends, but it sort of felt like a date. I'd been fond of her for some time but we were just friends, and that was okay. Nevertheless, we spent a ton of time together and one evening, we decided to catch some drinks post-work.

Things began to spiral after that. Jump to later that very night, and we both were sleeping at her place. During that week, I'd been having some poor-quality sleep, due in part to her pulling me out with her. When I'm not well-rested, I tend to have peculiar dreams, accompanied by sleepwalking or talking.

In the dream, I was strolling through a tunnel—resembling a metro passage. A girl was sobbing on the floor, completely naked. As I asked what was wrong, she abruptly attacked me. She resembled a zombie or something, and clasped her corpse-like limbs around me.

I managed to fend her off, and began shouting. This was my dream experience where I was battling for my survival. But what transpired in reality was fairly awkward. She tried to snuggle up to me, to which I overreacted and literally tossed her off the bed.

She shrieked, waking me up to an extent, although I was still very much consumed by the dream. She inquired about what was wrong, and I just blurted out—”Who are you? Where are your clothes? Get away!” I fully woke up as she stormed off the room.

She concluded I was acting foolish, I guess. I felt dreadful. I believed I'd messed up. However, after explaining the whole situation, she found it funny and returned to bed. But she doesn't miss an opportunity to tease me about it.

Young couple are seating on bed in bedroom.Kampus Production , Pexels

46. Talk About Weird

So there I was, on a first date with this girl. We kicked off the evening having a lovely dinner, and honestly, I could feel a spark. We decided to end the evening with a movie, but we missed our top pick by a whisker. Our remaining options were Scream and some action-packed Sylvester Stallone flick. We decided to go with Scream, why not, right?

The theater was filled with movie-goers who seemed to enjoy conversing with the on-screen characters—seriously, it was pretty loud. It was such a contagious vibe that I found myself joining in. I won't lie, I ended up hollering "DON'T ANSWER THE PHONE!" with half of the crowd.

After the credits rolled, however, she hardly spoke a word to me. Strangely, I never heard from her again. Either she realized I was too amazing to handle and felt she couldn't trust herself around me, or she was turned off by the fact I'd become one of those movie screen talkers and turned as dry as the Sahara desert.

Couple is watching a movie at cinema.Pavel Danilyuk , Pexels

47. A Narrow Escape

After more than a month of playful flirting, I finally decided to take this girl out. She seemed really into me all evening—she couldn't keep her hands off me. I thought to myself, "Awesome, looks like I've found a cool girl to spend more time with."

But then, right before the date was about to wrap up, her boyfriend suddenly shows up—absolutely out of the blue! We had been shooting pool for a good four hours by then. Seeing her boyfriend take over, I decided to quietly redeem my ID from the counter and just leave.

A few hours later, she rang me up, berating me for ruining the date. I could only retort, "You have a boyfriend. What date are you talking about?" It turns out, the bill for the pool table had spiked over 200 bucks because her boyfriend ripped the felt on the table.

Talk about dodging a bullet.

Woman is watching a man playing snooker.Ketut Subiyanto ,Pexels

48. Let The Ink Dry First

During our dinner date, a woman who had recently divorced sprang some unexpected news on me—she had kids. This was only made known to me mid-meal! Things accelerated unexpectedly from there onwards.

Suddenly, she was discussing me meeting her children immediately, the possibility of us living together and similar topics. All this, on our very first date! The idea of becoming a step-parent straight off the bat, especially so soon, was not in my plan.

Despite the awkwardness, we completed our dinner and said our goodbyes on good terms. We managed to have a sincere conversation and understood where we both were coming from. She admitted getting a little carried away with the refreshing thrill of singleness and dating again. 

She agreed that she should allow herself some time, letting the dust settle on her divorce before introducing new parters to her kids. Not too long after, we lost touch.

Man is smiling and having lunch with woman at restaurant.Gary Barnes, Pexels

49. Oops, Botched That One

During our coffee rendezvous, we decided to have a bite to eat. As our food is making its way to us, he whips out what looks like a vintage Nokia phone. In an attempt to add a dash of humor, I chuckle, "WOW, that's the most ancient phone I've come across recently!"

I really pushed the joke, intending to keep the atmosphere lighthearted. But alas, I had put my foot in my mouth big time. You see, it wasn't a Nokia phone after all. It was his insulin pump.

Woman is making a surprised face.Andrea Piacquadio, Pexels

50. What A Buzz

When I was around the age of 20, I found myself on a date with a girl who caught my eye in every way possible. She was just my kind of girl and I was over the moon about it.

Our meetup took place at a nearby pub, and things were going splendidly. It was crystal clear she was interested—there was plenty of hand touching and other positive cues. An unforgettable hour passed and a bathroom break was needed.

After washing my hands, I tried to use the hand dryer, which was out of order. Part of its protective grill was sort of dangling off. I wanted my hands dry for more hand-holding sessions with her.

Then, in what I would term as the most irrational decision of my life, I figured, "Hey, I could fix this!" and shockingly stuffed my hand right into the dryer's nozzle. WHAT WAS I THINKING!?

Unsurprisingly, I was zapped by the hot heating element inside. The shock sent me toppling back and my head hit the wall behind. Though I didn't black out, I needed a little while to gather myself before joining my date again. I just didn't have the nerve to tell her the truth about my foolish mistake.

Now nursing a throbbing headache and feeling a bit off, our date took a turn. It wasn't long after that she found a reason to leave. I later got turned down when I offered her a second date.

A year or so after this fiasco, I learned from her friend that she had really liked me but thought I was acting strangely odd when I returned from the restroom. She had quoted, "I'm not interested in dating someone on drugs."

Young woman is looking sad seating on a table.MAD_Production, ShutterstockSources: Reddit,

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